


Summer Time

by assbuttintheimpala



Series: A Summer Affair [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - Human, Anal Sex, Blow Jobs, Bottom Castiel, Feminization, Infidelity, M/M, Size Kink, Somnophilia
Language: English
Status: Completed
Published: 2013-06-09
Updated: 2013-06-09
Packaged: 2017-12-14 10:24:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,736
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/835837
Author URL: https://archiveofourown.org/users/assbuttintheimpala/pseuds/assbuttintheimpala
Summary: <blockquote class="userstuff">
              <p>It was the final summer before Castiel Milton was off to college and he knew he wanted to do something before he left. Maybe it would be more correct to say someone</p>
            </blockquote>





	Summer Time

**Author's Note:**

  * Translation into 中文 available: [Summer Time 盛夏时节](https://archiveofourown.org/works/5420870) by [destielarmyCN](https://archiveofourown.org/users/destielarmyCN/pseuds/destielarmyCN)



> This may have been inspired by a post I read in a forum while I was researching for another fic

It was the final summer before Castiel Milton was off to college and he knew he wanted to do something before he left. Maybe it would be more correct to say _someone._  Castiel was gay and he had known this for a while now he just hadn't had the opportunity to do anything with anyone.  
  
Castiel's sister, Anna, had a boyfriend for a while now by the name of Dean Winchester. He would come over every so often and hang out with Anna but Castiel hadn't had much to do with him as he had been busy with school work and college applications but now it was summer and Castiel had nothing to do until college started.  
  
Dean was incredibly handsome, Castiel noticed. The man was well built with broad shoulders and large biceps. His sun kissed skin brought out his bright green eyes that had flecks of gold around the pupil. Dean was five years older than Castiel and hadn't bothered with college as he had elected instead to stay at home and get a job at the local auto-shop. He overheard him telling Anna one day that he had used most of his pay check to buy his little brother, Sammy, new clothes and couldn't take her out till after next pay which Castiel found strangely endearing.  
  
To put a long story short, the only thing Castiel didn't like about Dean was how he always called him 'princess'. The nickname only came about because of the time Dean first came over to the house. Castiel’s youngest sister, Rachel, had asked him to join her for a tea party and because Castiel loved to please his younger siblings he had graciously accepted. Of course, a tea party with a six year old meant that it was dress up and Castiel found himself seated at a knee high table wearing a tiara and pink veil. It was shortly after the first cup of tea had been poured that Anna walked in to introduce her new boyfriend. Dean hasn’t let Castiel forget it since.  
  
One hot summer day, Castiel was lounging next to the pool in their backyard. His parents were rich and their home was more of a mansion. The size of the house was necessary however with the amount of siblings Castiel had. Including himself, there were eight Milton children and he was the fifth eldest with three younger siblings. Only he, Anna and his younger siblings, Inias, Samandirel and Rachel were left living at home. Lucky for him, they weren't big on swimming so he found his alone time by the pool.  
  
With his eyes closed, aviators on and wearing nothing but his swim trunks, Castiel was getting a healthy tan. He was almost about to drift asleep when he heard someone jump into the pool. Castiel shifted his head and opened one eye to see who the disturber of the peace was. To his surprise it was Dean.  
  
Castiel watched as Dean swam a few laps around the pool before he made his way to the side and leaned over to look towards Castiel before he quickly turned his head and paid attention towards the house. Castiel was glad he wore aviators because he was free to ogle at Dean without being caught. He tried not to move too much and pretend he was still asleep so Dean didn't catch him looking over. It was hard to tear his gaze away however as he watched the water drip down from Dean's soaked hair and over his tanned shoulders. Castiel could feel a semi popping in his trunks and had to finally close his eyes and think of something else just so he didn't pop a boner in front of Dean.  
  
When everything went silent and Castiel's dick had calmed down, he opened his eyes just in time to see Dean pull himself out of the pool. Castiel had to hold back a gasp as he watched all the water drip down Dean's muscular torso. His gaze followed one particular droplet all the way from the base of Dean's neck, past his collar bone, over his pectorals and down his sternum before it reached the trail of hair towards Dean's swim trunks. He couldn't help himself but follow the trail down to see the trunks Dean was wearing. They were navy blue and the damp fabric clung to him leaving nothing to the imagination which had Castiel's dick once again paying attention. But before Castiel could close his eyes and think of something else, Dean grabbed his towel which had been discarded on the clay bricks on the pool side and disappeared back into the house.  
  
When Dean was finally out of view, Castiel let out a deep breath and adjusted himself in his shorts. He was not about to jerk off to the thoughts of his sister's boyfriend. Not outside in the open anyway.  
  
Several hours later, the family, including Dean, were seated at the dining room table eating their dinner. Meal times were always a strange affair at the Milton household simply due to the fact that hardly any of their family got along. They were always arguing and fighting over the simplest things. It had however died down immensely when his oldest brothers – Michael, Lucifer, and Gabriel – had left home. Castiel had stayed out of the drama somewhat even when his older siblings had been around and was glad he was going to be finally free of it all when he was off to college. Just a few more months and he would be free.  
  
The odd thing about this meal however was that Dean was sat opposite him. Castiel had tried so hard not to stare and remember what he had seen earlier that day but it was found to be extremely difficult. He made sure to look away whenever Dean looked up at him. He didn't want to freak the guy out with his stares like he did so many of his classmates at school.  
  
"I am not going to argue on this, Anna. Dean will not be sharing your room tonight. Not under my roof and he definitely won’t be driving home in this rain" Castiel's mother said. A freak thunderstorm had started outside and it was raining heavily. "He can share a bed with Castiel because I will _not_ have him in a spare room where he can just sneak back into yours. At least with our Castiel in the bed, he won’t be tempted to sneak out." Castiel blanched as his mother spoke to Anna. Sharing a bed with Dean? Oh god this was not happening. "You don't mind do you sweetie?" Castiel's mother asked him.  
  
Castiel swallowed the lump in his throat as he looked dumbfounded between Anna and his mother refusing to look at Dean. Anna looked furious at her mother and his mother looked to Castiel with soft eyes which guilt tripped him into agreement. He quickly shook his head not able to trust his words at that moment and looked straight down at his meal to quickly finish it. Once he was done, he still had to stay seated as he tried to will away his half hard cock that had been present since the proposal of Dean sleeping in the same bed as him was announced. He really didn't think he was going to control himself tonight.  
  
Later, he was wrapped up in his bed wearing nothing but his briefs. Even with the rain outside it was still incredibly hot. He was too excited to go to sleep with the prospect of Dean coming in soon. He was getting horny just thinking about Dean lying next to him. Finally after what seemed like hours, Dean came into the room.  
  
"You awake, princess?" Dean asked into the dark room.  
  
"Yes, Dean. I'm awake" Castiel replied while he tried to keep his tone steady the use of the nickname helped somewhat.  
  
Dean closed the door and moved towards the bed. "Good don’t have to be quiet then" He said as he removed his shirt slowly. Castiel couldn't help but wonder if Dean was giving him a show. Castiel could feel himself getting harder under the covers as he watched Dean slowly undress. He definitely wasn’t going to be able to sleep with Dean next to him all night. Dean removed his shoes and socks along with his jeans and threw them haphazardly across the room revealing his tight black briefs with a huge bulge. Castiel watched as the man absentmindedly squeezed his cock and adjusted himself.  
  
Castiel's heart pounded in his chest as Dean slid in next to him and placed his arms above his head. Their legs were touching under the covers due to the small size of Castiel's bed and Castiel felt his dick twitch at the feel of Dean’s leg hair brush against his skin.  
  
"Go to sleep, princess" Dean said to the quiet room.  
  
Castiel turned away from Dean and lay on his stomach to hide his growing erection. He didn’t know if he was thinking with his dick, his hormones or his brain at that moment but he secretly agreed with himself that as soon as Dean was asleep, he was going to take advantage of the opportunity before him.

When Castiel finally heard Dean’s breath become deep some time later, he knew the man had fallen asleep. During the time it had taken Dean to fall asleep, Castiel had not moved an inch in worry that he would prevent Dean from falling asleep and he would have to wait longer. The wait had done nothing, however, to Castiel’s erection as he tried to will himself from humping into the mattress or even Dean.

With careful movements, Castiel turned to his side to face Dean and found that the man was indeed asleep. The man before him looked tranquil as he slept as if all the worries that plagued him while he was awake disappeared as he slumbered.

As he tried to calm his own breathing, Castiel raised a tentative hand and moved it towards Dean under the covers. When his hand grazed against Dean’s thigh, he quickly pulled it back unsure if Dean had felt it or not. When there was no reaction, Castiel watched Dean’s face as he moved his hand back over towards Dean this time he rested it on the muscle. To Castiel’s relief there was no reaction from the sleeping man.

The adrenaline started to pump through Castiel’s veins and with it his movements become bolder.  He cautiously slid his hand up Dean’s thigh towards his briefs. When his hand met the soft cotton, the teenager’s hand slid up and across to where he knew Dean’s bulge would be. His hand made contact with the piece of flesh through the cotton and Castiel had to bite his bottom lip to hold back a groan. Dean was huge and he wasn’t even erect.

Apparently, the shy, timid Castiel was gone and all he wanted to do now was to see how big Dean could get. As his hand made careful movements over his bed mate’s package, Castiel could feel the flesh warm and twitch beneath the cotton and he could feel his own react. With his free hand, Castiel moved to feel the front of his own briefs and almost let out a keen as he felt the wet patch of pre-cum while his hand relieved some pressure.

Castiel’s gaze had not once left Dean’s face as he monitored for any signs that the man was about to wake up. With the member almost erect beneath his hand, Castiel couldn’t help but feel the need to really touch it. Slowly, Castiel’s hand moved to the waist band of the man’s briefs and pulled it down to the comatose man’s thighs which freed the flesh to Castiel’s hand.

Quickly, Castiel took the member in hand and pulled lightly just like he usually did to himself. It was the first cock Castiel had ever touched that wasn’t his own and that thought caused another bead of pre-cum to drip from his own, now achingly hard, member.

Once he realised that Dean had not even stirred to the ministrations on his crotch, Castiel’s actions grew a little reckless as his need to see what he was dealing with grew. With as much composure he possessed at that moment, Castiel whipped back the covers so that both their lower regions were exposed to Castiel’s gaze. When Castiel saw that Dean still hadn’t reacted, he chanced a glance down to see Dean’s member in the flesh. Castiel almost came on the spot as his thoughts were confirmed. Dean had one huge cock. It not only had length but it had girth too and Castiel really wanted to know what it would feel like inside him.

Of course Castiel owned dildos and would secretly get himself off with them at least once a day. He was a teenager after all and he had needs. But once he had seen what Dean’s cock looked like, he didn’t think his dildos would ever satisfy him again as he knew that Dean had a much bigger girth than any of the dildos he possessed.

When Castiel’s hand resumed it slow massage of Dean’s cock, a bead of pre-cum pearled at the tip and Castiel had the sudden urge to know what Dean tasted of.

Slowly, Castiel raised himself onto all fours and moved towards Dean. He tried to even his weight out so the bed wouldn’t dip too much as he inched closer towards his bed mate. Once he was close, Dean suddenly let out a snort as his legs spread wide. Castiel froze and stared at Dean’s face but the man was still dead to the world. A smirk crossed Castiel’s face as he saw that Dean’s legs were now spread wide enough for him to kneel between. Dean had made it easy for him and he was in no state of mind to hold back.

Now positioned between Dean’s legs, Castiel had a full frontal view of Dean’s hardened member. It stood tall with drops of pre-cum spread down the member from where Castiel’s hand had been moments ago. With all caution thrown to the wind, Castiel licked the drop that was currently beaded at the tip. Once again, Castiel had to hold back a groan as once it hit his tongue, Castiel a goner. Dean tasted amazing and Castiel _needed_ more.

Without further hesitation, Castiel wrapped his mouth around the huge cockhead and swirled his tongue. More pre-cum released from the tip and Castiel licked it up hungrily. Castiel was completely caught up in the musky scent and taste of Dean to care about anything but getting more out of him when all of a sudden there were hands wrapped in Castiel’s hair. The teenager froze where he was unable to move. Dean was awake and knew what he was doing. Castiel’s heart pounded in his chest. How would he explain this to Dean? ‘Yeah I wanted to suck your cock so I waited till you were asleep to do it’. There was no way he was going to be able to explain this to anyone. He knew Dean would tell Anna who in turn would tell the whole family. Castiel was done for. His family wouldn’t pay for his college tuition now and he would have to leave the family home and find some dead end job living in a crappy one bedroom apartment hardly able to keep afloat.

Suddenly, Dean’s voice interrupted his thoughts “Mmm princess, feels good. Keep going”

Indecision flew out the window as Castiel knew he would never get a chance to do this again so he went to town on Dean’s dick. He had obviously never done this in the flesh, but he had placed his dildos in his mouth from time to time to trial the motion out. He had also read a lot of articles and forums on how to do the perfect blowjob and now he had an opportunity to try it out for real.

He sucked hard on the head and swirled his tongue which caused a groan from the man beneath him and the hand in his hair to grip tighter. The action made Castiel’s dick rise again after his brief worry. Castiel tried to get his mouth as low as he could onto Dean’s shaft but once he hit his gag reflex, he had to pull back.

“Princess, turn around for me. I want to see your perky little ass.” Dean whispered down to him.

Castiel didn’t think twice as he spun himself around. The cock in his mouth never left his tongue. Dean’s hands made quick work of Castiel’s briefs as he slid them over his ass and down his legs to fling them across the room forgotten.

“Damn, princess,” Dean began as he massaged Castiel’s cheeks “you have a nice ass”

Castiel moaned in pleasure around Dean’s cock at the words and ministrations to his ass which earned a small groan from the larger man. When spit slicked fingers grazed over his hole, Castiel gasped before he keened in pleasure. The motion made him suck harder on the cock in his mouth as he wanted to please Dean the best he could even if it was his first time doing so.

“Look at your tight little pussy, princess. Anybody been in here before?” Dean asked as his dragged his fingers along the cleft of Castiel’s ass.

Castiel shook his head as best he could around the cock in his mouth. He reluctantly pulled away knowing Dean wouldn’t have been able to tell what Castiel was trying to say. “No” Castiel groaned as Dean’s finger slipped over his entrance again “Only… only toys” Castiel panted

His answer caused a chuckle from Dean “Guess I’ll have to show you how good the real thing is huh princess?”

Castiel groaned and almost came just from the thought “Please” Castiel begged. He wanted to lose his virginity and he wanted to lose it to Dean. He knew he was betraying his sister’s trust but fuck, Dean was here and obviously willing so who was Castiel to deny the opportunity. In hindsight it was a selfish and heartless thing to deceive his sister like that but he wanted it so bad and without doubt he was going to get it.

“I’ll give you what you need” Dean soothed as he continued to rub one of his fingers up and down the cleft of Castiel’s ass while his other hand massaged his cheek “You got lube ‘round here, princess?” he asked

Castiel nodded and pointed to his bed side table “Top drawer at the back” Dean’s hand left Castiel’s ass and he almost whimpered at the loss before he remembered that Dean’s dick was still in front of his face. He quickly resumed his ministrations to Dean’s member as he wanted to show Dean he was eager for what was to come. He sucked as hard as he could and moved one of his hands to play with Dean’s balls.

A hand found its way into Castiel’s hair and petted him slightly “Easy there princess. Don’t want this to finish too soon now do you?”

Castiel reluctantly pulled away from Dean’s dick and savoured the taste of the pre-cum on his tongue while he committed it to memory. He more than likely wasn’t ever going to get another chance to do this so he needed to remember every detail.

Once Dean’s cock was free of Castiel’s mouth, Dean moved and sat up behind Castiel with his hands on Castiel’s hips. Castiel look back in confusion before he realised that it was time for the main event.

“Move down princess. Ass in the air” Dean commanded which aroused Castiel even further. He knew he wasn’t going to last long once Dean was inside him. Castiel was quick to oblige to Dean’s instruction and pressed his face into the bunched up comforter at the base of the bed while his ass was in the air under the scrutiny of Dean’s hungry gaze. He would have been embarrassed if he hadn’t have been so unbelievably turned on by the fact that soon he would have Dean’s dick inside him.

A gasp escaped Castiel’s mouth when he felt a cold, slicked up finger run over his rim. It was another first to have someone else’s fingers inside him and he was going to relish every moment. When the finger slid inside, Castiel let out a deep groan. Dean’s fingers were a lot bigger than his own and although the sensation didn’t hurt it was slightly uncomfortable. Soon enough, the feeling had changed into pleasure and Castiel began to rock back on to the finger. The motion earned a chuckle from Dean.

“Eager are we?” he teased but Castiel didn’t have it in him to reply he was too caught up in the sensation.

Another finger was added and stretched Castiel’s entrance wider. Castiel’s hands were now clenched in the comforter as he tried to calm himself as he didn’t want to come so soon but it had begun to be unbearably difficult. The sensations were too much and he had to slide a hand to grip the base of his own dick just to keep his orgasm at bay. He wasn’t going to come until Dean was inside him.

“Opening so good for me, princess.” Dean praised “Can’t wait to be inside this tight pussy of yours” Castiel wasn’t one to like feminization but god did it sound good as it came from Dean. He groaned and rocked back onto the digits in his ass as he tried to will Dean to go faster.

“Please” Castiel begged again one hand still firmly held onto the base of his dick as the other still clenched at the comforter. His face rubbed into the fabric as he tried to distract himself from the pleasure that shook through his body. “Hurry” he pleaded

“Shh princess” Dean soothed once again “Patience. I’ll give you what you need” With that final word, another finger was added and Castiel felt fantastically full and he didn’t even have a cock in him yet. It sent a thrill through his body as the reality of what was to come sank in.

Just as Castiel didn’t think the pleasure could get any better, Dean crooked his fingers and struck Castiel’s prostate which caused his back to arch and a sob be released into the comforter. Castiel had to turn his head to muffle all the sounds that tried to escape as even though the house was quite large, he didn’t want to risk being heard.

All of a sudden, the fingers were gone and Castiel felt empty. He hole clenched around the emptiness and he turned his head back to see what Dean was up to. He saw just in time as Dean slicked himself up and gave his member a few strokes. He was still hard and leaking and a shiver passed down his spine and the thought of it inside him.

Castiel moved his hand from his dick to clench the comforter as Dean’s hands gripped his hips again. “You ready, princess?” He asked to which Castiel simply nodded unable to speak.

The pain was excruciating as Dean’s head slipped past the rim and stretched Castiel impossibly wide. Dean groaned as he slid inside and Castiel had to hold back the sobs that threatened to escape. He wanted to enjoy this. He wasn’t going to get another chance.

As Dean slid in slowly, inch by inch, Castiel tried to focus on the pleasure instead of the discomfort. He focused on how Dean filled him and how it had felt to have Dean’s cock beneath his hand and in his mouth earlier; what he had tasted of and how he smelt. It seemed to work as Dean was abruptly bottomed out with his balls pressed against Castiel’s ass checks.

“Your pussy is so fucking tight” Dean panted while his hand rubbed up and down Castiel’s spine. Castiel concentrated on the gently gesture as the pain started to subside and he adjusted. “You okay princess?” Dean asked

Castiel nodded into the comforter before he turned his head slightly so he could speak “Give me a minute” he panted “You’re so big” the comment earned another chuckle from Dean and Castiel revelled in the fact that he had made the man laugh. He had a beautiful laugh and if Castiel didn’t have a huge cock in his ass distracting him, he would’ve turned and looked at Dean’s face to see him smile.

After what seemed like hours, but was more than likely only a few minutes, the pain subsided and Castiel slowly began to gyrate his hips to test out the pain. When he didn’t feel much discomfort other than a dull ache, he knew he was ready for Dean to thrust and he made it known. He rocked his hips further back before he whispered “I’m ready” back towards Dean.

Dean gripped Castiel’s hips tight as he pulled back almost all the way before he slammed back in. Castiel groaned at the feeling. It was infinitely better than having a toy inside him. Dean thrust again and Castiel groaned in unison with Dean.

“Your pussy feels so good, princess” Dean gritted out and Castiel decided to make it even better and clenched around Dean’s hardness. “Fuck” Dean groaned which caused Castiel to smirk into the duvet. “Not going to last like this. So fucking good, princess”

Dean’s thrusts grew erratic and the sound of flesh pounding against flesh filled the room. Castiel was a writhing mess and his dick was fully hard again as Dean pounded into him. It grew way too much and the sensations overpowered his senses unable to feel anything but Dean’s huge dick in his ass while he pounded away. A hand found its way to Castiel’s head once again and pushed him into the mattress further and Castiel revelled in the rough treatment. He didn’t know he could get so turned on from this but he didn’t want it to stop.

“So close,” Dean gasped as he pounded harder and harder.

When Dean finally changed his angle slightly and hit Castiel’s prostate, he cried out loud and his back arched. It was all too much for him and he could feel his orgasm building again. He didn’t bother to hold himself back this time however as he knew Dean wouldn’t be far behind. The thrusts were unrelenting against his prostate as Dean knew he had hit it.

Without warning Dean, Castiel came untouched over the bedspread beneath him while he squirmed and writhed under the pleasure. His senses were overwhelmed and he saw nothing but white as he rode out his orgasm. When he came to, he could feel Dean’s thrusts lose their rhythm and Dean cried out his own orgasm as he spurted his load inside Castiel.

Dean collapsed on top of Castiel’s back before he buckled under the extra weight and sprawled onto his belly on the mattress. He could feel Dean’s hot breath on the back of his neck and it sent another shiver down his spine.

Their breathing had finally returned to a somewhat normal pace when Dean finally removed himself from Castiel’s back and pulled out of Castiel’s hole. Castiel winced at the feeling before he felt cum trickle out and down his balls. He wished he had a plug just so he could force it back in as a reminder of what had happened.

There was a light nudge to Castiel’s side and he turned his head to see what Dean wanted.

“Come on, princess” Dean whispered and lifted him to turn him around. He gently laid a boneless Castiel back onto the bed the right way around before he turned Castiel onto his stomach to ease the burn that he felt in his backside. Castiel watched through half-lidded eyes as Dean pulled the comforter back over them and lay back down. “Go to sleep, princess” Dean whispered as Castiel succumbed to his exhaustion.

When Castiel awoke the next morning, Dean was gone and all that he had to remind him of the events was a painful rear end and cum on his sheets.


End file.
